The anti-interview series that dives deep into the quirky crevasses of designers, illustrators and typographers. DQSD consists of fun tales and hilarious anecdotes from the most talented creatives around the world.

Steven Heller is as prolific as it gets in the design community. Steven has worked with Tom Wolfe, interviewed Milton Glaser; He is a luminary, forging graphic design’s archival history. And we bet you never knew whether or not he was a cat person.

He was an art director for the NY Times for 33 years. He has published over 170 books on design and popular culture. He is the co-founder and co-chair of the MFA Designer as Author program at the School of Visual Arts, New York, where he lectures on the history of graphic design.

Heller is the recipient of the AIGA Medal in 1999, the Art Directors Club Hall of Fame Special Educators Award in 1996, The Pratt Institute Herschel Levitt Award in 2000, the 2011 National Design Award for Design Mind, and the Society of Illustrators Richard Gangel Award for Art Direction in 2006. With Heller’s cascade of books, articles, lectures, conferences, exhibitions, courses, blogs, radio essays, podcasts, and rants and raves, he labors mightily to help find a foundation under the eclectic range of activities that designers practice.

It doesn’t matter whether Mr. Heller considers himself an actual designer or not, this was a special interview.

You’ve interviewed a ton of people. Is there one person in particular that you haven’t that you’d want to interview?

Sara Blakely is the founder of Spanx. There isn’t a woman (or man) in this world that hasn’t heard of Spanx or thanked their lucky stars that it was invented. Just for those of you that have lived under a rock the past 10 years, Spanx is the revolutionary undergarment, that turned into a global sensation. The story of Sara’s success is all about simple innovation. With a single, disruptive design idea, she changed an entire industry and created a new product category.

What would your first thoughts be if you were asked to write Grease 3?

If he isn’t consulting on new ideas and new businesses, he is shaping the future somehow. He was one of the first designers to agree to our dumb questions, and we were lucky enough to catch Josh on the hook, and get him to take part in our funny little game. We can’t thank him enough for his expertise and his patience.

When compiling our list of people we want to interview, there are always a few names we never think will answer, either because they are super famous or super busy, or both. Ashleigh Axios agreed to do our ‘Dumb Questions’, demonstrating that designers are a strong, affable community, and that Axios herself is one of its biggest proponents.

Imagine trying to please both the Federal Government and the American people. Essentially that is what Ashleigh does, proving design is a carefully constructed tool, and she wields it with both strength and humility.

Needless to say, she has a lot on her plate. After all, she is the Creative Director of the White House. The freaking White House! Axios is a designer, a maker, a wife, as well as the President of AIGA’s Washington DC chapter.

In the spirit of powerful design, we cut through some actual, tangible red tape for this one, and her answers are brilliant, insightful, funny, smart and impressive. We are glad design in politics is proving its value and growing in importance. Thanks, Ashleigh.

If you’re going on a road trip with President Obama, what kind of car would you drive?

Matthew Manos wants to change the way businesses do business. Manos is the Founder and Managing Director of verynice, a global design-strategy consultancy that ignites movements, builds brands, and challenges perspectives. verynice has a very unique business model; the company gives half of their work and time away for free to nonprofit clients.

Jean Jullien is arguably the most famous artist in the world right now. His ‘Peace for Paris’ has become a worldwide symbol of support.

Mostly, Jullien’s work tends to have a light and breezy, sometimes on-the-nose humor. He has made a habit of reacting to the news in drawings before, from the Michael Brown shooting in Ferguson to the legalization of gay marriage in Ireland and even the Charlie Hebdo shootings in Paris last january, but a simple, slightly off-kilter rendering of the Eiffel Tower framed by a circle so as to look like a peace sign has taken the world by pacifistic storm.

If you had to get trapped for a month in one city’s subway system which would you prefer, NYC or London?

Bradford Shellhammer is a colorful badass. He has been named one of the ‘100 Most Creative People in Business’ by Fast Company, coined the ‘King of Quirk’ by Forbes Magazine, and the ‘Eames of E-Commerce’ by USA Today.

As chief design officer of Fab, the design-obsessed flash-sale site he co-founded in 2011, Shellhammer was instrumental in changing the way online consumers shop and navigate. In March of this year, Shellhammer launched Bezar, the definitive marketplace for design. It is a way for designers to sell directly to consumers. This isn’t Fab 2.0, this is much more intricate with a sharp eye for detail, personal taste, and just simply making items accessible to everyone, like Ikea.

It was an absolute blast to interview Mr. Shellhammer. Here are his smart answers to our dumb questions.

Since your name sounds like that of a superhero, what would be the name of your arch nemesis?

Todd Radom is a team player…quite literally. He is a slugger, a sports branding expert, a craftsman, and a historian. He has become endemic to sports culture.

Radom has done logos for just about every big event in American professional sports. Todd’s work includes the official logos for Super Bowl XXXVIII and the 2009 NBA All Star Game, as well as the graphic identity for Major League Baseball’s Washington Nationals and Los Angeles Angels.

Among the leading designers in the professional sports industry, his two decades of work with the NFL, NBA, and Major League Baseball have resulted in some of the most familiar icons of our popular culture.

The baseball season just came to an end with the Kansas City Royals defeating the New York Mets to win the World Series, perfect timing for us to score a DQSD interview with the king of sports iconography.

World Series, nationally televised, do you feel confident throwing out the first pitch?

Aaron Draplin is a damn good designer. His company, the Draplin Design Co., has worked with brands like Esquire, Nike, Red Wing, Hughes Entertainment, Wired, Coal Headwear, Patagonia, Burton Snowboards, and Ford Motors. When the Obama administration needed help on a logo for the DOT Tiger Program & Recovery.gov, they called Draplin.

On top of all the killer design work he has done, he then went and created Field Notes, a notebook for anyone with a back pocket and an idea. Through Draplin’s blood and sweat, he took the mundane concept of a notebook and made it into a necessary tool.

Behind the lumberjack myth, he is a simple man. He loves working, he loves junkin’ and he loves music. All in all, he is super nice and down-to-earth, a guy you’d want to grab a beer with, and simultaneously complain about and celebrate the world. Sidenote: I just ordered myself one of those badass Draplin Design Co hats.

Jon Contino is New York. We caught him on daddy day while his daughter was playing with Play-Doh in the background. The phone interview couldn’t have been more perfect. His voice has that New York snare to it, complete with the cadence of traffic trailing off over a bridge into another borough. As you may know, he specializes in old school lettering with new school flare; that may be putting it too simply. Hard work and history permeate every fiber of his aesthetics. The dude revels in the imperfections of old ink and paper. He has done work for giants like Nike, 20th Century Fox, Miller High Life, even the Sports Illustrated Swimsuit Issue. He loves hard music, the Yankees, his wife and his daughter. Other than that, he is just a super nice dude, and we are thankful for letting us get to know him with our dumb questions.

Would you rather be the brand manager or general manager for the Yankees?